Jenny Leander

Jenny had felt the familiar wetness between her legs, as she had looked at the perfect white buttocks of the young boy. She felt sorry for him, but she also recognised the inevitable sexual excitement she felt when she was about to start a punishment.

On instinct she had put the strap on the floor and moved forward behind him. With an almost delicious sense of control she had placed her hands on his buttocks and slipped her fingers between the tightly clenched cheeks of his bottom. She plied the quivering flesh apart, hearing him gasp at the sudden intrusion.

Jenny had always had a penchant for dominance, ever since she could remember. Her appointment to the center had been heaven-sent. She had been able to indulge her pleasures, legally and with the full blessing of the state. Her greatest thrill was when there were no witnesses to the beating, other than the regular attendance of the center's office workers and essential personnel.

Jenny loved the embarrassment of the young boys. Seeing their tear stained faces colour up to a deep crimson always sent a thrill through her body. She relished each scream; basking in the total control she had over the young offenders.

When she had come to the center she had realised that all of the girls who worked in close proximity to the offenders, where very much like herself. Many, she knew, had been attracted because of their enjoyment in dominating young males. Even those that had joined without that predilection, had soon found deep within their inner psyche, that they were sexually excited by strappings.

The center encouraged as many of the office workers as possible to attend the beatings. Their presence always caused further embarrassment to an already humiliating experience for the young boys. Jenny knew that most of the girls who watched the punishments were soon wet with excitement as a boy was soundly and expertly thrashed.

The routine never varied to any great extent. But often after the boy had been punished the pad would be removed and the bar would be raised with the boy's feet being spread apart and fastened securely. If there were no visitors waiting to inspect her handiwork then she would stand behind him and reach around to take his penis in her hand, before milking him mercilessly until he reluctantly ejaculated. She would exacerbate the humiliation of the young offender by talking to him as she vigorously worked on his penis. "Well… you only have yourself to blame, fancy having to have your bottom smacked by a girl."

It was often the case that the miscreant seemed to form some sort of a bond with his tormentor… and to her delight, the further embarrassment of being chided and masturbated by her, caused them profound embarrassment.

It had been a long time since she had seen a boy seem to suffer his punishment so badly, She was aware that some boys had particularly sensitive flesh and it was obvious from this young man was one of those.

She had administered the strap, as she always did, covering him with lashes from thigh to the very top of his buttocks with the first six and for the second six, overlaying each stroke as she saw fit. She always gave the last three strokes on the center of the buttocks, each aimed to precisely fall on top of each other. She knew that even with the hardiest of boys that the pain was intense… but she reasoned that after all that is what they were here for.

She had seen Debbie show concern at the state of the boy, but had not lessened the severity of her strokes, once she had been given the go-ahead to continue.

Well sweetie, she thought. I am sure that between us all we will make it up to you. She smiled at the delicious thought as she watched the warders unfasten his legs and remove the extension and the pad from the horizontal bar.

She could hear him groan as the horizontal bar was raised mechanically so that he was able to stand upright. His feet were fastened ensuring his legs would be spread wide apart. His arms were still fastened to the horizontal bar and his head was resting on the top of the padding which covered it.

She could see that his buttocks were badly blistered as he shivered and shook with the intensity of his pain. She knew that she would not be able to indulge in any other activity today as there were many more visitors here than usual, including a senior and two junior judges. It was common practice for the witnesses to stand around an offender after he had been punished. Often they would chide him, sometimes taking hold of his penis or his testicles as well as running their hands, sometimes roughly, over his freshly blistered bottom.

She watched Debbie as she approached the boy, gently stroking his cheeks as he stood there, sobbing in agony and anguish.

It was the senior judge who first got up from her chair. She approached the boy and standing in front of the padded bar, gently held his head in her hands. Jenny could not hear what she was saying, but the judge's actions seemed tender almost loving as she spoke with him. Jenny watched as the judge patted the boy on his head and then walked around the upright bars to examine his bottom. To her surprise and delight, the judge bent down between his widely spread legs and reached through his parted thighs. Jenny held her breath as she saw the judge lifting his penis and gently cupping his testicles.

The judge held him there for several moments before letting him go. Abruptly she stood up and went to stand beside Debbie. Jenny was far too curious to let the conversation go unmonitored. She put down her strap and joined Debbie and the Judge who greeted her warmly. "I was just telling Sister Pearson, that he seems to have taken his punishment badly. She has agreed to keep him here for a few days in the recovery wing. I know you all have your duty to do, but I did wonder if perhaps you might take special care of him." Both Debbie and Jenny smiled at the judge's request. It was Debbie whom replied. "I think we can take very special care of him. You are right, I think he has taken it very badly and I understand that he lives alone, so there is no-one else to look after him. If you would like… you could see him in, say a couple of days. In fact I won't release him until you ask me to, how's that?"

The judge smiled. "Yes I think he is erm… rather special and certainly not our ‘run of the mill' customer. Yes if you would… I er… would be most grateful." The judge looked around to see that most of the all female audience were already leaving their seats; some were already standing around the boy as he sobbed pitifully. Jenny saw that one of the girls had nonchalantly reached down and taken hold of his penis, stroking her other hand over his back in a comforting gesture. Jenny knew that the statutory half hour of confinement after a punishment was a painful time.

But she knew that most of the girls were cognizant of the court transcript and of the boy's circumstances and she could already see that their attitude was one of tenderness and sympathy towards him.

My scream lasted until my voice gave way. The timbre of my own voice had sounded surreal to my ears, as if I was in an echo chamber. I cannot think how long it had been since the last stroke; it was a while before my fevered brain realised that perhaps at last my punishment might be over. I could just see through my tears a blurred image of female faces watching me.

I shivered and shook, the pain had not diminished. I had not thought that any human could endure such pain. The severity of my beating had shocked me to the core. I shook in fear as I became aware of movement around me, fearing that my beating was to start again. Instead I felt gentle hands against my waist and my legs as the straps of my confinement were removed from my ankles and waist. I breathed deeply, not able to quell my sobs of pain and self pity as the padded rest was taken from under me.

I stood shaking as I felt the bar beneath my head and arms begin to move slowly upwards and gentle hands prompted me to move my shaking legs forward. I felt a firm grip around each of my ankles as I was prompted to shuffle my feet apart, until I was standing with my legs spread wide. The bar continued to rise until I was able to straighten my back.

I felt a huge tremor of fear as I felt straps being placed around my ankles to hold my legs in position; I wondered if my new position was to afford me more punishment. I gasped in anguish and pain not knowing what was to happen to me, only knowing that my body could not stand any more hurt.

I started to cry in despair and anguish as I stood spread legged with my head resting against the soft pad. I must have been near to fainting; as if in a dream I saw the beautiful face of Debbie Pearson. I felt her hand gently stroke my cheek, her face full of concern as she looked at me. My emotions were so stretched that I was overwhelmed by the gesture, I cried, sobbing mightily. My chest heaved and I gasped for breath in between the huge sobs that wracked my body.

I stood there for what must have been several minutes, my mind clearing from the acute pain of the last three strokes of the strap. I was aware of movement in the room and of someone coming to stand in front of me. I raised my head sufficiently to see that the lady judge was standing before me. Suddenly I felt her hands gently hold my head so that I was looking into her eyes. She spoke softly and tenderly as I sobbed pitifully.

"Well Stephen, your physical punishment is finished. I know that you are in pain, but it will ease in time. I am going to inspect your bottom and check that you have not been marked anywhere else. I am not going to sign your release until your bottom has been properly treated. I understand that you live on your own. Do you have anyone that could care for you when you are released?"

Somehow I managed through my sobs to answer her. "Er… no one… er miss… er Ma'am.

She looked at me closely; I could see the tenderness and concern on her face, which only prompted me to cry even more.

"Well in that case I will see what I can do. I will see you again Stephen, when you are more recovered." I sobbed as she gently stroked my cheek before taking her hands away. I stood with my head resting on the bar again as suddenly I felt soft delicate fingers gently lifting my testicles and to my horror, the shaft of my penis being gripped firmly and the foreskin being fully retracted so that the skin was stretched tight. I felt helpless and humiliated as I tried to look around behind me, but could only see as far as the interested expressions on the faces of the young girls and women as they got up from their seats.

I closed my eyes in shame as I felt my penis and testicles suddenly being squeezed firmly before being let go. I sobbed at the pain in my buttocks and the humiliation of my public naked punishment. I felt dejected and shamefully aware that all the girls in the room had witnessed my naked bottom being soundly strapped and heard my cowardly screams and anguished cries for mercy.

I stood sobbing with my head resting on the padding, aware that I had been surrounded by some of the girls from that had witnessed my punishment. Two of the younger girls were standing in front of me. I tried to stifle my sobbing but to no avail as they looked at me, their pretty faces showing their curiosity at my predicament. One of them put her hand to my cheek and spoke quietly to me. "My name is Jane and this is Karen… don't look away when we are talking to you." I groaned with shame… my tears still rolling down my cheeks as I raised my head from the pad.

"My, you must be in pain… It must be really humiliating for you, having your bare bottom spanked in front of so many people." I felt her other hand gently touch my chest, her flattened palm stroking gently downwards until her fingertips were just touching the top of where my pubic hair used to be.

"I bet you feel really ashamed of yourself don't you? I mean what about little willy here…" her hand moved downwards over my smoothly shaved skin. Deliberately she curled her fingers around my penis and pulled it forwards and upwards.

"Fancy not even being able to have your modesty covered while you were being spanked!"

I groaned in humiliation as the other girl brushed her fingers delicately across my chest, teasing my nipples, at the same time reaching down with her other hand and curling her fingers under my testicles. I had never felt so vulnerable as her fingers enveloped my scrotum and she lifted and weighed my testes in her slender fingers. Her voice was soft but teasing as she spoke to me.

"What a shame it must be for you… and you being such a nice looking boy. You feel really smooth down here… why don't we just stiffen you up a little bit mmm? Make all that hurt go away, shall we?"

I groaned in despair and desperation as Jane took both hands to my penis and held the tip of the glans between finger and thumb so that she could slide the foreskin down the shaft. There was a mischievous look on their pretty faces as I felt their delicate fingers expertly manipulate my penis and testicles: I tried to look away, but everywhere I looked there were girls watching me with interested looks on their faces. I could feel soft hands stroke over my back and upon the inside of my thighs as other girls began to touch me. Everyone seemed to have gathered together to watch the two girls stimulate my genitals.

I could feel an answering throb in my penis as my foreskin was expertly slid up and down the shaft. I could not help shivering as she stretched the foreskin skin tightly each time she retracted the covering of the glans. Her skilful fingers gave me no respite as she looked at me, her pretty face smiling knowingly as my penis became engorged in her hand.

"My… he is a cheeky little fellow isn't he… and he's growing nicely. Does that feel nice mmm?" Her fingers moved faster as my penis began to stiffen rapidly. I felt my cheeks suffuse in a deep blush as suddenly she took her hands from my engorged flesh and began to tap her hands upwards against the shaft. I groaned with embarrassment as I felt it bob up and down. I could not look down but I was well aware that my penis was now fully erect and throbbing visibly. The pain from my buttocks seemed to enjoin with the acute sexual sensation in my penis, reluctantly making me as hard as I had ever been. I felt Karen reach her other hand between my legs and gently scrape her fingernails along the underside of the perineum; the combined sensations of their fingers eliciting even greater sexual sensation.

Jane looked at me as she slipped her fingers back around the shaft of my penis. "Well sweetheart… you are a big boy now, even if you don't have any hair. We are going to let you go, so that the other girls can have a look at this nice long fat willy of yours!" She gripped the flesh of my penis hard, at the same time as Karen squeezed my testicles firmly in both hands. She pressed her pretty face against mine and whispered. "If I had my way… I'd stick my finger up your bottom and milk that beautiful penis of yours and make you come all over the floor." She smiled innocently as she moved her head back and looked at me… "you'd like that wouldn't you, my little bare baby?"

For the next twenty minutes, I endured humiliation after humiliation. Soft delicate hands, examined my body… probing stroking and stimulating me at will: their softly spoken words of tenderness and comfort spurring me to even greater sexual awareness and embarrassment. I could not have contemplated a more embarrassing situation, each girl adding to my shame with her touch or her words. My penis kept to a painfully exquisite hardness, jutting out and upwards from my body in a reluctant shameful display.

Suddenly it was all too much for me. I began to sob loudly in utter misery, tears rolling unhindered down my cheeks. I felt comforting hands holding me around my waist as my legs and arms were freed.

I stumbled rather than walked between the two warders as they led me to a small room with a padded bench. A shiver ran though me as I saw the thick leather strap which hung down from each side of the bed, one half had a leather covered buckle and the other was perforated with a series of holes. The sight was foreboding after my experience in the punishment room.

Through my tears I could see that there was a hole, of about six inches in diameter in the centre of the bench as they bade me first kneel… and then lay face down upon the linen covered surface. I was placed so that I was laid flat upon my tummy, my erect penis and my swollen testicles, hanging freely through the hole in the padded surface. I shivered as one of the tall beautiful warders slipped her hands underneath the bed and casually took hold of my penis and testicles. Her voice was tender and caring; "There is a pan underneath you, so if you need to urinate, just do it. You are not to move at all… you do understand? Someone will come and put something on your bottom, I won't cover you in case it aggravates your skin and I am not going to fasten you down with the restraint.

I wish I could do something for this…" she squeezed my penis more firmly, but I am afraid that I am not allowed to." She squeezed my penis once more and then let me go.

I felt the other warder lift my head and hold a glass of water to my lips. I found myself drinking greedily until my dry throat was quenched. She took the glass away and gently slipped a slim pillow underneath my head. She bent forward and softly kissed my tear-stained cheek. "Try and rest… it has been a traumatic time for you. If you can… try and sleep… at least until Sister Pearson comes and does you little bottom for you."

I was still blushing profusely from the casual handling of my genitals as they both left the room. I heard them stop for a moment outside of the room and became aware that the lights were being dimmed. I was left in solitude and semi-darkness as I contemplated my sorry state. I wanted to try and rub the hurt from my bottom cheeks, but was afraid that if I touched them they would become more inflamed. I felt naked and vulnerable as I lay, my uncovered, upon the soft surface of the bench, my penis and testicles hanging down freely exposed to the sight of anyone who entered the room. My trauma and fatigue got the better of me and I drifted into a light sleep… for a time, remembering nothing more.

I awoke sometime later as I felt soft hands being gently smoothed over the tender cheeks of my bottom. A cooling and soothing liquid was being sensuously applied over my burning buttocks and thighs. I was aware that the lights had been turned up to full brightness and that all four of the nurses were standing around my bed as well as Sister Pearson. I must have stirred as I heard her say. "Shhhhhh Stephen…. Don't say a word, just lie there and we will be finished soon. I felt her hands gently encase my penis and testicles which were hanging down through the hole in the padded bench, her slippery fingers expertly retracting my foreskin, making me raise my buttocks at the suddenness of the acute sensation. "Shhhhhh… just relax now." Again Sister Pearson quieted me as the gentle hands of one of the nurses, soothed over my bottom. "I am going to milk your penis and empty these for you." She illustrated her words with a gentle squeeze of my testicles as she began to slip her hand quickly up and down the shaft of my penis.

I groaned in a mixture of embarrassment and sexual sensation as I felt more hands being placed upon my bottom. Two of the nurses were now caressing and soothing my buttocks, one of the nurses slipping her fingers in and out of the crevice between my cheeks as Sister Pearson deftly brought my penis to an erect state. Deftly she retracted the foreskin fully and let her fingers slide quickly up and down over the rim of the glans. Instinctively I raised my buttocks with in reaction to the acuteness of the sensation, only to feel a finger slip unhindered inside my bottom. I tried to raise my body up, only to feel the hands of the other two nurses gently press on my back and shoulders.

One of them leaned over my head and kissed me softly on the cheek. "Shhh… Stephen, just lay still now." Her gently spoken words were in contrast to the busy fingers that were expertly manipulating my penis and the slippery slender digit that suddenly curled skilfully inside my bottom. "Argggghhhhhhhhh" I groaned as my prostate gland was explored with a firm pressure from the nurse's finger. I felt the Sister hold quickly my penis with two hands as the one of the nurse's let go of my shoulders and moved closer to the Sister. I heard gentle whispering but could not make out what was being said as the nurse also slid her arms underneath the bed and took hold of my testicles. I felt them being held firmly as Sister Pearson slipped my foreskin back with one hand and rubbed over the very tip of my penis with the other.

I was in a turmoil of sexual sensation as suddenly my prostate gland was prodded firmly, this expert attention was accompanied by a second finger being thrust up through my sphincter as my buttock cheeks were casually spread open by the nurse who was massaging my buttocks to allow the other nurse greater access.

"Aarrrrrggghhhh." I shook my head as I felt my sphincter being stretched impossibly wide and my penis being rapidly milked, the Sister's hands moving over my engorged penis in a practised motion.

"Relax now… it won't take long… be a good little boy!" The soft voice of the Sister added fuel to my abject embarrassment and feeling of helplessness. My shame knew no bounds; to be systematically thrashed and humiliated in front of so many beautiful girls and then to be expertly drained of semen in a nonchalant and casual display of expertise, had humiliated me beyond my comprehension.

My mind reeled in dismay, my shame tantamount to a deep and bottomless despair.

I was acutely embarrassed at the thought that I could not contain the sudden acute sensation from deep within my groin. It was the inevitable humiliation as I felt the inextricable point of no return; the unyielding sensation that heralded the beginning of my ejaculation. No respite was given as my bottom was explored thoroughly by the nurse's probing fingers buried deep inside me; nor by Sister Pearson who milked me so expertly that I lost all sense and reason.

"AArrrgggghhhhhh. Oooooohhhhhhh… arrrggghhhh." I groaned as semen spurted spontaneously from my penis; again and again I ejaculated… my tumultuous orgasm agonisingly prolonged by the skilful fingers of the Sister and her nurses.

"Poor baby… never mind it will all be over soon… just a little more... there we are what a brave boy." The tender voice of the Sister inflamed my senses as her hands seemed to stimulate the very core of my nervous system.

For the second time I was being milked with such skill and expertise, that I felt I could not withstand the acuteness of the sensations that were being so dexterously wrung from my body. My chest heaved as I fought for breath, I gasped as my penis continued to spurt huge globules of semen without respite. The sensual pressure upon my penis and the firm incessant probing inside my bottom, held me suspended in the throes of utter and inexorable sexual abandonment.

"Arggghhhhhh. Please don't… no more pleeeeaaaseee"

I could not contain my emotions; such was the skill of the nurses and the sister that I felt I would die with the severity and the intensity of the feeling that coursed through my body… an exquisite mixture of unbearable pleasure and pain.

I raised my shoulders in panic as I reached the limit of my endurance, only to feel gentle hands press me back down upon the bed.

There we are… my you are in a state…shhhhhh now…" The soothing voice of the Sister did little to assuage my utter nervous exhaustion. My sinews seemed locked in a deep convulsion, my neck and throat constricted in a trancelike grimace. My penis pulsed so violently that I could feel a deep ache between my legs.

"ARRGGGGHHHH." I groaned in protest until at last the hands of the nurses and the Sister simultaneously slowed to a gentle caressing touch.

I had been drained, thoroughly and efficiently… expertly milked of every last drop of seminal fluid. I could only gasp at the acute sensation as the nurses fingers were slipped slowly out of my bottom, my sphincter being stretched in one last exquisite agony, as Sister Pearson stilled her fingers upon my penis … and squeezed the rigid flesh reassuringly.

"Poor baby… it has all been too much for you, hasn't it? Never mind… just relax and you will be fine." I felt soft hands caressing the hair at the back of my neck and soft delicious lips upon my cheek as the nurse held her pretty face close to mine.

It was with a feeling of utter exhaustion that I felt my penis being gently squeezed and wiped with a hot towel. Two pairs of hands were delicately applying more soothing ointment to my buttocks and thighs, while the other nurses stroked their slender fingers, in light feathery touches, over my back and shoulders. My last recollection as I drifted back to sleep was the dimming of the lights and a cool cotton sheet being drawn over my body, covering me up to my shoulders.

It must have been sometime during the night that I awoke as I felt the strap being tightened around my waist, the pressure immediately forcing my hips flat against the bed. The lights had been turned up to full brightness and I blinked as I became fully awake.

Before I could protest I heard the soft voice of the young receptionist and felt her hand gently brush against my face.

"Shhhhh… I am not going to hurt you. Just lie still." To my embarrassment I felt her lift the sheet from my feet and slowly and deliberately slide it up over my shins and thighs, eventually baring my bottom totally. She casually folded the material over the strap which was fastened around my waist.

For some reason I felt even more naked and vulnerable than If I had been totally uncovered. Feeling utterly helpless, I was forced to lay flat with my buttocks bared and my hips pressed firmly against the surface of the bench by the broad waist strap, my penis and testicles fully exposed as they hung down through the hole. I tried to look at her as she stood behind me, but the broad strap stopped me from twisting my body far enough for me to see her.

Instead I lay my head back on the pillow, with my head turned to the side. I felt utterly stupid with my bottom bared as if I were a small child. I squeezed my legs together as tightly as I could and tried to clench my buttocks, but the movement caused my skin to burn with pain as I tensed the muscles.

I knew she was examining my buttocks, but could do nothing to stop her. I lay there in silence until she moved further up the bed. I gasped as her hand reached under the bed and casually fondled my penis and testicles. The almost nonchalant way that she handled me, made me feel even more vulnerable and embarrassed. She took her hand away, after pulling my flaccid penis downwards, stretching it to its full extent.

I watched as she moved to stand in front of my face which was turned towards her. She placed her hand between my cheek and the pillow, gently turning my head so that she could look into my eyes.

I felt my face begin to burn as the blood rushed to my cheeks in a deep flush of embarrassment. She noticed my blush instantly and smiled at my discomfort, giving me a knowing look. Her eyes twinkled behind the slender framed glasses, making me feel utterly foolish as I lay fastened upon the bench with my bottom bared for her inspection.

"Right, the same rules apply. You don't speak unless I ask you a question. When I ask you a question you answer me immediately. Don't try and turn your head away and don't be evasive with your answers. When I ask you to do something, you obey immediately. I know Sister Pearson has put some ointment on your bottom, which will have relieved a lot of the pain. However, a sharp slap with my hand upon those little cheeks of yours will still hurt you more than you can imagine. So… tell me…do you understand me?"

I could not help blushing to an even deeper red as I looked into her eyes, her pretty face looking amused as my face burned with shame.

"Er… yes miss… er I understand.

"Good… now, are you going to obey my instructions immediately and without question?"

I looked at her, feeling utterly foolish as she held my head so that I could not evade her cool appraising gaze.

"Er yes.. miss… I will try."

I felt utterly foolish under the control of a girl younger than myself… and yet knew that I was in no position to argue.

"No… you will not TRY to do as you are told… you will DO as you are told… now have you got that?"

I blushed again, but managed to stammer a reply. "Yes miss… I will do as you ask."

She let go of my cheek and stood back, looking at me for a few moments, before moving out of my sight to stand at the foot of the bench.

I felt her cool fingers grasp each of my ankles.

"Right… bend your knees and draw them up as high as you can." She illustrated her instructions by pushing my ankles forward. I groaned with humiliation as I drew my knees up, until they were hanging over each side of the narrow bed. She had held my ankles together so that the soles of my feet were touching each other.

I felt utterly humiliated as I realised the vulnerability of my position. I was no longer able to clench my buttocks together and I knew that she would be able to see into the crevice of my bottom. She continued pushing on my ankles until my thighs were widely spread apart. I gasped in dismay as I felt her fingers gently trail over the under-part of my bottom cheeks.

"Well Stephen… you certainly have a well spanked bottom, just what naughty boys need. Did it hurt very much when you were being given the strap?"

I was already blushing profusely from the humiliating and revealing position of my legs. I could feel her hand move freely in-between the crevice of my bottom; the casual touch of her fingers accenting the openness and availability of my sphincter to her touch.

"Answer me; you are in no position to disobey without incurring an extra little smack on this naughty bottom of yours!" She punctuated her words with a tap on the inner part of my bottom cheeks, thankfully not touching any of the skin that had been beaten with the strap.

I groaned with humiliation as I answered her. "It was awful er… miss I didn't think I could stand it… I felt as if I …"

I could not finish the sentence. Whether my tears were of self pity or just the culmination of the events of the day, I did not know… but I began to cry.

"Yes… naughty boys always seem to cry when their bottoms are soundly spanked… however you can save your tears. Tell me which part of your punishment was the worst?

My voice trembled as I answered her. "The last strokes miss, it… it was like I was being er… branded miss. It was the worse thing I have ever felt miss."

I felt her hand move from in-between the cheeks of my bottom and her fingers trail delicately over the welts on the centre of my bottom.

"Yes… she has done an excellent job of strapping your bottom for you, hasn't she?" I could tell by the tone of her voice that she expected an answer.

"Er… yes miss…arghhhhh." I gasped as the tender flesh seemed to burn under her touch.

"Still tender… isn't it?"

"Yes miss." I replied gasping as she placed her hand casually back in-between the cheeks of my bottom for a moment, before taking her hand away.

"Well Stephen, I am afraid that is what naughty little boys deserve. I firmly believe that young boys should be soundly spanked regularly and of course, milked diligently rather than letting you indulge in that disgusting habit that boys have of playing with their own penises. Now just relax your bottom, while I just stiffen you up a little bit."

I blushed at the way she talked to me as if I were a small child. I also felt utterly embarrassed at the thought that she could do with me as she wished.

I felt her fingers return to invade the crevice between my buttocks; this time they felt cold and slippery.

"Arghhhhhhh…ohhhhhhh." I gasped as she pressed her finger firmly against my sphincter, impudently teasing the small rosebud of muscle by moving her finger up and down over the opening.

"Just relax like a good boy. Ooops there we are, now that's what I like… now let's just slip it all the way in for you… just keep your little bottom still."

"Argggggghhhhhhh….oooooohhhhhhhh please nooooooo." I could not help groaning and protesting as she slid her finger deftly and easily up into my bottom. My position made it impossible for me to clench my buttocks. I felt utterly helpless as she quickly located my prostate gland and expertly smoothed her finger over the sensitive mound.

"Arrrrrggggggggghhhhhhhhhhhhhhhhhhhh." I could do nothing but groan and cry out as I felt an incredible pressure building up deep within my bottom. I tried to move only to feel her slap the lower part of my thigh.

"Don't you dare try and evade me… just lie still like a good boy while I make your penis nice and stiff… there now that seems to be working nicely." I groaned and moaned as her finger moved quickly and diligently inside me. I could feel my penis throb as her finger roamed unhindered inside my bottom, expertly coaxing me to a full erection. I gasped when her wrist touched the blistered skin of my buttocks as she moved around to the side of the bed: her finger remained firmly in my bottom and not missing a beat as she reached underneath me.

"Ooohhhhhhhhh." I could not help crying out as she casually took hold of my penis between finger and thumb, squeezing to examine the stiffness, while at the same time prodding my prostate gland with the tip of her finger.

"There we are… all nice and stiff in no time. Little boys are sp predictable… and you have stiffened quicker than all of them… my word Stephen, what a dirty little boy you are. Don't you feel embarrassed that your penis stiffens so easily? What a naughty, naughty child, you have obviously had no proper control in your life, you really deserve to be soundly spanked. Have you no shame?"

I was utterly mortified as she chided me, helpless and humiliated and blushing so profusely, as her words reduced my stature to that of a small child.

She took her fingers away from my penis and firmly pressed her finger downwards stretching my sphincter widely.

"Just relax that bare bottom of yours… ooops there we are, just a little push now…try and relax now… take a deep breath sweetheart."

Her words were accompanied by an even firmer pressure from her finger. "Arggghhh….oooooooooooooooohhhhhhhhhhhhhh.

I gasped as something large and hard was pressed against the opening before being slipped deftly and firmly up into my bottom.

"Ooooooooooooooooooooohhhhhhhhhhhhhhhh." I tried to evade it but could not move. I cried out in anguish as the cool hard object was slowly and firmly introduced deep into my anus. The increasing girth stretching me widely until she finally located the device in an agonising pressure against my prostate. She withdrew her fingers leaving my bottom firmly impaled.

"Arghhhhhhhhhhhhhhhhh… er ohhhhhhhhhh pleeeeeeeeeeease misss…. er oooohh."

I gasped and moaned as she reached her hand underneath the bench and again felt the hardness of my penis with her finger and thumb.

"O.K. sweetheart, I am going empty these balls of yours… hold tight now!"

I could only gasp not knowing what she was going to do. For an instant I felt her soft fingers near the crease of my bottom and then suddenly a firm and incessant throbbing against the very core of my penis. The sensation was so acute that I felt my hips tremble and my legs shake in abandonment as I cried out.

"Arrrrrrgggggggggggghhhhhhhhh," My abject wail of anguish went unheeded as the device vibrated methodically against my prostate. I could not contain my emotions as her hands enveloped my penis and testicles. I felt the skin of my foreskin being stretched back as the movement of her fingers seemed to join with the incessant throbbing deep within my bottom.

What she was doing to my penis I did not know… the sensation was so intense that I was incapable of coherent thought. The expert manipulation of her fingers upon my captive flesh gave me no respite. Just when one movement became almost bearable she changed; pinching or squeezing the sensitive flesh in such a way that she almost seemed to have a telepathic knowledge of exactly what I was feeling.

"You are going to come soon… what a naughty little boy you are… aren't you ashamed of yourself?"

Her voice sounded casual, almost mocking in its tone, the steady modulation in contrast to my utter degradation and anguish as her fingers callously manipulated me to a pitch of sexual torment.

Such was her skill that I did not feel one of her hands momentarily leave my penis, but I knew that she must have adjusted the device in my bottom as it suddenly throbbed with even greater vigour.

"Arrrrrrrggggggggggghhhhhh… oooooohhhhh."

I arched my back in a painful concave arc, lifting my shoulders from the bench and throwing my head back as the device pulsed quickly and solidly deep within me. Her hands seemed to be touching every nerve of my penis as I ejaculated reluctantly and violently. "aarrgggghhhhhhhhhhhh… pleeeease…nooooooooooooooooooo" My pleading and shameful anguish at the intensity of my orgasm elicited no mercy from her. I was being milked so thoroughly that I felt I would die of sensation.

"There we are… what a big brave boy you are… just a little more now… you are not finished just yet." Her words seemed to spur my ejaculation to even greater vigour as her hands gave me no respite from the intensity of my orgasm.

"There… what a good little boy… let me have it all and I will turn the vibrator off for you."

I felt her fingers firmly milk my penis in a downward motion and squeeze hard as she reached the tip. Soft fingers touched my bottom for a moment and then suddenly… utter relief as the throbbing in my bottom ceased.

Her hand reached back underneath me and I felt my testicles being squeezed as once again my penis was milked in a deft downward movement. I lay my chest back upon the bench, gasping for air as her hands began to move slowly over my genitals, caressing my penis and testicles with feathery touches.

My throat felt hoarse as I gasped and groaned, while she steadied my emotions with gentle touches; her fingers carefully avoiding the sensitive glans and rim of my penis.

"Sensitive little fellow aren't you? Never mind sweetie… its all over now! Just lie still for a moment and I will take the vibrator out of your bottom and then you can straighten your legs. Hold still honey…. there that's the way… take a nice deep breath now."

I felt her hands gently pry my buttocks more widely apart and then suddenly, the incredible pressure of my sphincter being stretched wide as the device was removed. My knees and legs ached as I straightened them to lie straight upon the centre of the bench. I shuddered in anguish and fatigue as she moved towards my head and laid her hand gently on my cheek.

"Poor little baby… a sound spanking and then having to be milked. What a shameful experience for you… and to think all because you were a naughty little boy!"

Her words were the final shame to my ordeal. Tears formed in my eyes as I felt her move away and thankfully relieve me of the constraints of the broad leather strap, before carefully covering my bottom with the sheet. My tears flowed freely as, moments later, I heard the door close and saw the lights being dimmed to a soft glow.